CN1221721A - Prepn. process of 2,2,2-trifluoiodoethane - Google Patents
Prepn. process of 2,2,2-trifluoiodoethane Download PDFInfo
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- CN1221721A CN1221721A CN 98122046 CN98122046A CN1221721A CN 1221721 A CN1221721 A CN 1221721A CN 98122046 CN98122046 CN 98122046 CN 98122046 A CN98122046 A CN 98122046A CN 1221721 A CN1221721 A CN 1221721A
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- preparation
- reaction
- trifluoro
- transfer catalyst
- chloroethane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for preparing 2,22,2-triflluoroiodoethane features that under the existance of quaternary ammonium salt or polyethylene glycol as phase transfer catalyst, the 2,2,2-trifluorochloroethane and one-valence metal's iodide take part in reaction in non-protonic polar solvent while heating them to generate 2,2,2-trifluoroiodoethane with high output rate.
Description
The present invention is a kind of 2,2, the preparation method of 2-trifluoro iodoethane.
As everyone knows, extensively be used as Kazakhstan dragon (Halon) compound of clean fire-fighting medium, owing to destruction to atmospheric ozonosphere, will be disabled in worldwide.And 2,2,2-trifluoro iodoethane is because it might be as the surrogate of disabled Halon fire-fighting medium.Therefore it is a very important compound.But up to the present relevant its report of preparation is actually rare.G.Drivon reported from HCFC-133a, prepare the method (PCT.Int.Appl.WO9,730,959) of this compounds by halogen exchange reaction, but its result is not ideal.Therefore, seek the surrogate of Halon, especially convert fluorine-containing alkyl chloride to fluorine-containing idoalkane in the hope of turning waste into wealth, being still the organic chemist has problem to be solved.The object of the invention provides a kind of from 2,2,2-trifluoro-chloroethane (HCFC-133a) preparation 2,2, the method for 2-trifluoro iodoethane.
The present invention is fixed from HCFC-133a, in aprotic polar solvent, generates product 2,2 by the reaction high productivity with monovalence metal iodide MI, 2-trifluoro iodoethane, and available following reaction formula is represented:
Wherein M is a metal.
Mol ratio 1 among the present invention between reactant HCFC-133a and the MI: 1-50 adopts more substantial MI, to not significantly influence of reaction result.From economic consideration, recommending mol ratio is 1: 3-10. monovalence metal iodide recommends to use NaI or KI.Reaction solvent is an aprotic polar solvent, as N, N dimethyl formamide (DMF), dimethyl sulfoxide (DMSO) (DMSO) and N-Methyl pyrrolidone (NMP) etc., catalyst for reaction can be the polyoxyethylene glycol (PEG) of non-proton type, and molecular weight can be 500 to 100000, and promptly specification can be PEG-500 to PEG-100000, also can be quaternary ammonium salt R1R2R3R4NX, wherein R
1, R
2, R
3Or R
4Can be C
1-15Alkylaryl or benzyl, X can be chlorine, bromine, iodine.The weight ratio of HCFC-133a and catalyzer is can be 1: 0.01-0.10.Further increase catalyst consumption reaction result is not had obvious influence.Temperature of reaction can be in 80 ℃ of-150 ℃ of intervals, when temperature is low, and speed of response is slower, thereby will prolong the reaction times.When temperature was higher, then by product 2,2, and 2-Halothane content increases 100-140 ℃ of recommendation response temperature.The reaction times of this reaction was generally 8-20 hour, and the continuation prolongation reaction times can increase content of by-products, and is unfavorable to reaction result.
Adopt preparation method of the present invention, can make things convenient for and high productivity with 2,2,2-trifluoro iodine monochloroethane converts 2,2 to, 2-trifluoro iodoethane is the method that is applicable to suitability for industrialized production.
To help to understand the present invention by following enforcement bar, but not limit content of the present invention.Embodiment.
Exemplary steps: in 2 liter autoclaves, add DMSO or the DMF of 800ml, 600g sodium iodide or potassium, and 10g catalyst P EG-2000, tighten autoclave after, vacuumize, add HCFC-133a 360g..120-130 ℃ of following successive reaction 14 hours, can get product 2,2 through aftertreatment, 2-trifluoro iodoethane.When changing above-mentioned various condition, reaction result is listed among the following table 1-4.
Table 1 sodium iodide amount is to the reaction influence
Sequence number NaI amount (g) temperature of reaction (℃) time (h) productive rate (%)
1 450 125 14 68
2 600 125 13 72
3 900 125 14 74
Table 2 catalysts influence sequence number catalyst agent weight (g) reaction temperature (℃) productive rate (%) 1 PEG-6000 10 125 72 2 PEG-2000 7.2 120 70 3 PEG-100000 36 125 71 4 butyl ammonium iodides 10 120 65 5 hexadecyltrimethylammonium chlorides 10 120 67 6 phenyl trimethylammonium bromides 10 120 60
The influence of table 3 solvent
Sequence number solvent reaction temperature (℃) productive rate (%)
1 DMSO 120 68
2 DMF 120 51
3 NMP 125 72
The influence in table 4 temperature of reaction and reaction times
The sequence number temperature (℃) time (h) productive rate (%)
1 125 14 72
2 100 20 61
3 150 12 58
4 125 10 59
Claims (6)
1. one kind 2,2, the preparation method of 2-trifluoro iodoethane, it is characterized in that in the presence of aprotic polar solvent and phase-transfer catalyst 2,2,2-trifluoro-chloroethane and monovalence metal iodide MI were 80-150 ℃ of reaction 8-20 hour, 2,2, the mol ratio of 2-trifluoro-chloroethane and MI is 1: 1-50,2,2, the weight ratio of 2-trifluoro-chloroethane and phase-transfer catalyst is 1: 0.01-0.10, described phase-transfer catalyst are quaternary ammonium salt R
1R
2R
3R
4NX or polyoxyethylene glycol, wherein R
1, R
2, R
3Or R
4=C
1-C
15Alkyl, aryl or benzyl, X=Cl, Br or I.
2. a preparation method as claimed in claim 1 is characterized in that described α, α, and the mol ratio of α-chlorofluoroethane and monovalence metal iodide is 1: 3-10.
3. a preparation method as claimed in claim 1 is characterized in that described molecular weight polyethylene glycol is 500 to 100000.
4. a preparation method as claimed in claim 1 is characterized in that described temperature of reaction is 100-140 ℃.
5. a preparation method as claimed in claim 1 is characterized in that described aprotic polar solvent is N, dinethylformamide, dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone.
6. a preparation method as claimed in claim 1 is characterized in that described monovalence metal iodide is NaI or KI.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB981220460A CN1182092C (en) | 1998-11-27 | 1998-11-27 | Prepn. process of 2,2,2-trifluoiodoethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB981220460A CN1182092C (en) | 1998-11-27 | 1998-11-27 | Prepn. process of 2,2,2-trifluoiodoethane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1221721A true CN1221721A (en) | 1999-07-07 |
| CN1182092C CN1182092C (en) | 2004-12-29 |
Family
ID=5227530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB981220460A Expired - Fee Related CN1182092C (en) | 1998-11-27 | 1998-11-27 | Prepn. process of 2,2,2-trifluoiodoethane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1182092C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107857691A (en) * | 2017-10-30 | 2018-03-30 | 大丰跃龙化学有限公司 | New method prepared by a kind of iodomethane of a fluorine one |
| CN113307720A (en) * | 2021-04-16 | 2021-08-27 | 浙江巨化技术中心有限公司 | Preparation method of 1, 1-difluoro-2-iodoethylene |
-
1998
- 1998-11-27 CN CNB981220460A patent/CN1182092C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107857691A (en) * | 2017-10-30 | 2018-03-30 | 大丰跃龙化学有限公司 | New method prepared by a kind of iodomethane of a fluorine one |
| CN113307720A (en) * | 2021-04-16 | 2021-08-27 | 浙江巨化技术中心有限公司 | Preparation method of 1, 1-difluoro-2-iodoethylene |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1182092C (en) | 2004-12-29 |
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